An insight into the synthesis of cationic porphyrin-imidazole derivatives and their photodynamic inactivation efficiency against Escherichia coli

Xavier Moreira; Patrícia Santos; M. Amparo F. Faustino; M. Manuela M. Raposo; Susana P. G. Costa; Nuno M.M. Moura; Ana T. P. C. Gomes; Adelaide Almeida; M. G. P. M. S. Neves

doi:10.1016/j.dyepig.2020.108330

An insight into the synthesis of cationic porphyrin-imidazole derivatives and their photodynamic inactivation efficiency against Escherichia coli

Xavier Moreira
, Patrícia Santos
, M. Amparo F. Faustino
, M. Manuela M. Raposo
, Susana P. G. Costa
, Nuno M.M. Moura^*
, Ana T. P. C. Gomes
, Adelaide Almeida
, M. G. P. M. S. Neves

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

Abstract

New porphyrin-imidazole derivatives were synthesised by Radziszewski reaction between 2-formyl-5,10,15,20-tetraphenylporphyrin 1 and several (hetero)aromatic 1,2-diones, which after cationization afforded promising monocationic photosensitizers 3a-d. Singlet oxygen studies have demonstrated that all the cationic porphyrin-imidazole conjugates 3a–d were capable to produce cytotoxic species. These photosensitizers were able to photoinactivate Eschericha coli and their inactivation profile was improved in the presence of KI.

Original language	English
Article number	108330
Journal	Dyes and Pigments
Volume	178
DOIs	https://doi.org/10.1016/j.dyepig.2020.108330
Publication status	Published - Jul 2020
Externally published	Yes

Keywords

Antimicrobial photodynamic therapy
Gram-negative E. coli
N-Heterocycles
Photosensitizer
Porphyrin

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10.1016/j.dyepig.2020.108330

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Moreira, X., Santos, P., Faustino, M. A. F., Raposo, M. M. M., Costa, S. P. G., Moura, N. M. M., Gomes, A. T. P. C., Almeida, A., & Neves, M. G. P. M. S. (2020). An insight into the synthesis of cationic porphyrin-imidazole derivatives and their photodynamic inactivation efficiency against Escherichia coli. Dyes and Pigments, 178, Article 108330. https://doi.org/10.1016/j.dyepig.2020.108330

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title = "An insight into the synthesis of cationic porphyrin-imidazole derivatives and their photodynamic inactivation efficiency against Escherichia coli",

abstract = "New porphyrin-imidazole derivatives were synthesised by Radziszewski reaction between 2-formyl-5,10,15,20-tetraphenylporphyrin 1 and several (hetero)aromatic 1,2-diones, which after cationization afforded promising monocationic photosensitizers 3a-d. Singlet oxygen studies have demonstrated that all the cationic porphyrin-imidazole conjugates 3a–d were capable to produce cytotoxic species. These photosensitizers were able to photoinactivate Eschericha coli and their inactivation profile was improved in the presence of KI.",

keywords = "Antimicrobial photodynamic therapy, Gram-negative E. coli, N-Heterocycles, Photosensitizer, Porphyrin",

author = "Xavier Moreira and Patr{\'i}cia Santos and Faustino, \{M. Amparo F.\} and Raposo, \{M. Manuela M.\} and Costa, \{Susana P. G.\} and Moura, \{Nuno M.M.\} and Gomes, \{Ana T. P. C.\} and Adelaide Almeida and Neves, \{M. G. P. M. S.\}",

note = "Funding Information: The authors are grateful to University of Aveiro and FCT / MCT for the financial support for QOPNA research Unit ( FCT UID/QUI/00062/2019 ), the LAQV-REQUIMTE ( UIDB/50006/2020 ), CESAM ( UID/AMB/50017/2019 ) and CQUM ( QUI/UI0686/2018 ) through national founds and, where applicable, co-financed by the FEDER , within the PT2020 Partnership Agreement, and to the Portuguese NMR Network. The research contract of N.M.M. Moura ( REF.-048-88-ARH/2018 ) is funded by national funds (OE) , through FCT – Funda{\c c}{\~a}o para a Ci{\^e}ncia e a Tecnologia , I.P., in the scope of the framework contract foreseen in the numbers 4, 5 and 6 of the article 23, of the Decree-Law 57/2016, of August 29, changed by Law 57/2017, of July 19. Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

year = "2020",

month = jul,

doi = "10.1016/j.dyepig.2020.108330",

language = "English",

volume = "178",

journal = "Dyes and Pigments",

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AU - Moreira, Xavier

AU - Santos, Patrícia

AU - Faustino, M. Amparo F.

AU - Raposo, M. Manuela M.

AU - Costa, Susana P. G.

AU - Moura, Nuno M.M.

AU - Gomes, Ana T. P. C.

AU - Almeida, Adelaide

AU - Neves, M. G. P. M. S.

N1 - Funding Information: The authors are grateful to University of Aveiro and FCT / MCT for the financial support for QOPNA research Unit ( FCT UID/QUI/00062/2019 ), the LAQV-REQUIMTE ( UIDB/50006/2020 ), CESAM ( UID/AMB/50017/2019 ) and CQUM ( QUI/UI0686/2018 ) through national founds and, where applicable, co-financed by the FEDER , within the PT2020 Partnership Agreement, and to the Portuguese NMR Network. The research contract of N.M.M. Moura ( REF.-048-88-ARH/2018 ) is funded by national funds (OE) , through FCT – Fundação para a Ciência e a Tecnologia , I.P., in the scope of the framework contract foreseen in the numbers 4, 5 and 6 of the article 23, of the Decree-Law 57/2016, of August 29, changed by Law 57/2017, of July 19. Publisher Copyright: © 2020 Elsevier Ltd

PY - 2020/7

Y1 - 2020/7

N2 - New porphyrin-imidazole derivatives were synthesised by Radziszewski reaction between 2-formyl-5,10,15,20-tetraphenylporphyrin 1 and several (hetero)aromatic 1,2-diones, which after cationization afforded promising monocationic photosensitizers 3a-d. Singlet oxygen studies have demonstrated that all the cationic porphyrin-imidazole conjugates 3a–d were capable to produce cytotoxic species. These photosensitizers were able to photoinactivate Eschericha coli and their inactivation profile was improved in the presence of KI.

AB - New porphyrin-imidazole derivatives were synthesised by Radziszewski reaction between 2-formyl-5,10,15,20-tetraphenylporphyrin 1 and several (hetero)aromatic 1,2-diones, which after cationization afforded promising monocationic photosensitizers 3a-d. Singlet oxygen studies have demonstrated that all the cationic porphyrin-imidazole conjugates 3a–d were capable to produce cytotoxic species. These photosensitizers were able to photoinactivate Eschericha coli and their inactivation profile was improved in the presence of KI.

KW - Antimicrobial photodynamic therapy

KW - Gram-negative E. coli

KW - N-Heterocycles

KW - Photosensitizer

KW - Porphyrin

UR - https://www.scopus.com/pages/publications/85081133592

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DO - 10.1016/j.dyepig.2020.108330

M3 - Article

AN - SCOPUS:85081133592

SN - 0143-7208

VL - 178

JO - Dyes and Pigments

JF - Dyes and Pigments

M1 - 108330

ER -

An insight into the synthesis of cationic porphyrin-imidazole derivatives and their photodynamic inactivation efficiency against Escherichia coli

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Keywords

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